The Assistant
by Falpalfever
Summary: Watch what happens when Jimmy's nervous new assistant makes a mess and gets rewarded. Warning: VERY MATURE ID LOVE TO HEAR WHAT YOU THOUGHT ON IT :)


I had been working at the Tonight Show for about a month now as a personal assistant, but every day that I went to work I was just as nervous as I was on the first day. This was Jimmy Fallon we are talking about. I had so many responsibilities but the most important of them all was to keep him happy.

"Hey pal! How's it going?" I heard him ask, striking up a conversation with a writer as he walked down the hall.

I quickly made sure that everything in his office was up to par. His favorite coffee was in it's rightful spot on the desk and his macbook powered on but not logged in because of course he likes his privacy. The giggly conversation came to a close and his nice wide and tall body sauntered into the room.

"Good morning Mr. Fallon!" I greeted him with a smile.

"Good morning Casey! And it's Jimmy! Im old but im not Mr. Fallon yet." He chuckled.

"Sorry Mr. F-I mean Jimmy. I'll remember that! Your coffee is ready for you and I spoke to Mr. Michaels this morning. He said he wanted to go over the premise of the new sitcom with you this afternoon at one-thirty. Should I push back your lunch with Mr. Timberlake?" I said throwing it all at him at once.

He sighed taking it all in and as he entered his computer password he answered "Uh-uh, tell Mr. Timberlake I'll be at lunch at one and tell Mr. Michaels that I will head up to his office in a few minutes so we can just get it done now." I could tell by his use of "Mr" and their last names that he was playfully mocking the way I sounded so professional.

I nodded my head and started to make my way out the door before he stopped me asking me to come look at a picture he had on his phone.

He flipped to the picture of his bubbling baby girl Winnie and his face lit up "Isn't she adorable! Oh my gosh!"

I stood next to him as he sat in his chair, his arm very close to my thigh. This was so wrong! I am supposed to be in awe at how cute his daughter is when all I could do was think about how I wanted him. I glanced at how his muscles looked in his casual thin sweater and how the bottom of his hair peeked into a little point at the top of his neck. I shifted myself away from him a little trying to fight the urge that my body was feeling. My planner fell to the floor and it snapped both of us back into reality. Jimmy quickly reached down to grab it at the same time I did so as he looked up, my breasts were right in his line of vision. He quickly looked away and handed me the planner. Nervously, I thanked him before taking it from his hand. He cleared his throat and reassured me that it was no problem. It wasn't until a writer came in a few seconds later that our eyes broke away from each other.

"Hey Jimmy!" The writer said casually

Jimmy stood up and greeted his friend with a hug. They stood there for a few moments talking about some game ideas that the writer had and Jimmy gave some suggestions on how to make it a little less serious and more about ridiculous.

"These are great! Casey will you get me that notebook over there so I can write these down?" Jimmy asked quickly.

I walked behind his desk and grabbed his notebook that he used for show ideas and a pen. As I reached for the pen near his coffee my hand knocked into the coffee and sent it flying all over Jimmy's pants and bottom of his shirt.

"Oh my god! I am so so sorry Jimmy! I-I didn't mean to do-oh my god! I am so sorry!" I kept apologizing.

Right thenI knew I was getting fired.

He looked down at the stain now on his pants and joked "I drink so much coffee that I just pee coffee now"

Both him and the writer chuckled as he looked to me.

"Please, don't worry about it! I have plenty more of these here and at home" he promised.

I went over to the phone on his desk and dialed the wardrobe department. I ordered a new pair of dressed down pants asap. The writer said he would just get with him later on the ideas and I raced to the wardrobe department to retrieve his pants.

—-

After what felt like an eternity I finally made it back to Jimmy's office with his new pair of pants. His office door was closed which in my one month at this job, never happened, so I hesitantly knocked.

"Who is it?" His voice asked kind of timid.

"It's Casey! I have your-uh-delivery!" I said not wanting to embarrass him.

"Oh great! Come in!" He ordered.

I opened the door to find him in his boxer briefs. I quickly looked away and felt like I needed to apologize. His face was tinted red with a bit of embarrassment grinned and thanked me.

"Sorry if this is awkward! I-I can leave if you wa-" I started with a shaky voice.

He interjected and assured me that it wasn't awkward and that he didn't mind if I stayed. I looked at him now, trying to keep focus on the upper half of his body, but soon my eyes ended up glossing over his lower half. His thick muscular legs emerging from a thin piece of tight material that stood in between me and his cock. With a quick second look I could see that he had it tucked away in his briefs to his left and I could also see the coffee seeped through onto that layer of clothing as well. I walked over to him as he noticed the stain. He sat down in his seat and I offered to help. I bent down to reach the water bottle that he had placed underneath his desk when I realized that my face was now within a few inches of his now growing cock. He moved his chair back and repositioned himself trying to hide the bump that was now increasing in size.

"Maybe it'll come out with some water" I suggested semi innocently.

I poured a tiny bit of water onto the stained spot on the upper leg and his face showed struggle in his attempt to restrain himself. I pat the area softly at first and then started rubbing the area, slowly working my fingers way up to his now bulging erection. He shot up and I quickly jumped, startled.

Before he could even say anything, I stood and exclaimed "Im sorry that was out of line. I shouldn't hav-"

A forceful kiss from him silenced me. Everything just felt so normal and so passionate. We both knew exactly what the others move would me. I hopped into his arms, wrapping my legs around him. He carried us to the door, locked it, then stumbled back to his chair. He sat in the chair, while I sat on his lap. His tongue gliding in and out of my mouth, as I would playfully bite and pull his bottom lip.

"Wait-I-Nancy wont-" He started contemplating.

As he was worrying I lifted my shirt and my tits bounced out of my shirt and into his face.

"Fuck it." He decided.

His mouth formed around my hard nipple and started sucking on it as his hands made their way to the small of my back. He unzipped my skirt and peeled my thong off with it. I felt his cock twitch against my inner thigh. I lifted his shirt and just had to take a deep breath once I saw the beauty of his chest. He was so wide because of his broad shoulders and his stomach was perfect in the way that it wasn't too hard from being full of abs but it was still beautifully toned. I felt his large hands trace their way down to my ass. He grabbed it with both hands and squeezed it as my hips started to rock back and forth on his. He grunted, trying to tell me he was ready. I slid off of his lap, underneath his desk and opened up the front of his briefs so that his hard on flung out of it's barrier. I looked up at him from under the desk with puppy dog eyes acting as if everything we were doing was innocent. It drove him wild. His cock was modestly sized but still way above average. I took the base of his shaft in one hand and jacked it with my other and my mouth caressed the tip. Soon I went from jacking him with my hand to mouth. My head bobbing back and forth viscously. His palm pressed against the back of my head guiding me on his cock. I finally ripped the briefs off of him and threw them onto the floor. I moved my hand to his balls and rubbed them around in my hand. They were so well taken care of and so soft. His seven inch long and very thick cock was a challenge to fit in my mouth but I knew I had to do it. His eyes shot open as he felt it fall into my tight throat. I felt his pre-cum leak into my throat and into my mouth. I looked at him wondering if he liked a spitter or a swallower. I swallowed, thats what he liked. He lifted me up and with one arm cleared all of the items on his desk. Suddenly, there was a knock on his door. He covered my mouth with his hand.

"Im in a meeting!" He shouted out.

We waited for a few seconds before we continued. His mouth left lingering kisses from my mouth down to my breasts, down my stomach, and finally ending at my pussy.

"Oh my god Jimmy just eat me already" I moaned.

I felt him blow on my clit and it drew me wild. Finally I felt the tip of his soft wet tongue separate my pussy lips and he began to suck on my clit. I pushed his head down redirected his tongue to my now soaking wet hole.

"Oh my god you taste so good" He complimented as his tongue circled my hole before shooting in and out of it.

"Take me Jimmy please. I can't wait anymore. I need you in me." I begged.

He moved us over to the much softer couch that he had in his office. I was now on top of him so I could position myself on his dick. I didn't want to tell him that I never had a cock his size in me before, but I knew he could tell from the expression on my face.

"I wont hurt you I promise." He said sweetly into my eyes.

I felt his tip raise up to my opening and it slowly made its way in. It was so soft and warm, all I wanted was the rest of him. His hands wrapped around me, he slowly helped me lower myself onto him. With every warm inch that went in me a shiver went up my spine. Once it was in I grabbed his face and started to kiss him once again. I ran my fingers through his thick beautiful hair as I moved up and down on him.

"Take control Mr Fallon. Be my boss!" I demanded.

He flipped me onto my back. He was now hanging over me as his cock went in and out. Faster, and faster, and faster.

"I want to fuck you so hard." He confessed.

I bit his lip and then seductively whispered in his ear "Well then, FUCK me hard."

Instantly his cock slammed in and out my tight pussy. I started rubbing my clit and I squealed out and he covered my mouth. He told me to shut up and I got so turned on by him dominating me. I sat back up and started moving my hips and circles on his while he thrusted in and out his mouth now on my tit again. His hand made its way down to my pussy and rubbed it quick as he went in and out. The sound of his balls hitting my ass filled the room. I could see in his face that he was coming soon. His jaw clenched and his chest tightened. Sweat emerged at his hair line. He rubbed me harder knowing that it would get me there too. My back arched and my nipples stood erect.

"James. Oh my god baby this feels so good. Jimmy. Yes! Yes! Jamessss" I moaned.

He watched me as I orgasmed as quietly as I could. It just kept going. He wouldn't stop putting it in and out of me. I never experienced an orgasm that many times in a row. He saw my cum shoot onto his long hard cock and it sent him over the edge as my pussy tightened around him. For years I fantasized what he looked like when he climaxed and now I was seeing it. His eyes open, watching my every movement then slowly rolling back with his head. His mouth open with my name escaping it multiple times. He is breathing heavily and then suddenly I feel his warm load enter me and his hands squeeze my back tight. It was my favorite feeling in the world. We both sat there, exhausted, looking into each others eyes.

"Let's get back to work." I giggled.


End file.
